Women have a lot to think about when shopping for a handbag. They want to find the perfect arm candy that they can truly connect with and exactly fits their style and budget. This article deconstructs the anxiety called the Handbag Decision Paralysis (HDP) that bugs most women who are in the market for a new purse.

FOR THE PAST SEVERAL MONTHS, I have been carrying a decidedly unglamorous bag to work. It’s a beige canvas tote that says Espolón Tequila with a picture of a skeleton riding a rooster. My husband got it free at an event. Nobody likes it.

As much as I would like to declare that I am making some sort of anti-fashion, pro-tequila statement, I have to be honest: This bag is not so much a choice as it is the consequence of not making a choice. Following some expensive missteps, and facing the recent explosion of beautiful options, I appear to be suffering from an increasingly common condition. Call it Handbag Decision Paralysis (HDP), a type of commitment phobia in the accessories milieu.

This past year, I first lusted after the near-ubiquitous Céline Luggage tote, then the very ubiquitous Proenza Schouler PS1—a trim, double-buckled satchel that seems to have colonized the first floor of Barneys’ Madison Avenue store, in all sorts of fabrications and hues. Most recently, I’ve been obsessing over the softly voluminous double-handled Givenchy Nightingale tote, which has similar cult status. I’ve wasted countless hours looking at images of bags online, emailing links to friends, debating the pros and cons of various color schemes and then wallowing in a shame spiral for spending so much time thinking about something as inconsequential as a sack in which to stuff my sorries. It seems I may not be alone.

Jennifer Zucher, co-founder of matchmaking service Project Soulmate, likens HDP to the dilemmas of dating. “Everyone thinks that the next person is going to be better than the last, and that’s why people don’t settle down,” she said. “It’s the same thing with bags.” She speaks from experience. For the past three months, Ms. Zucher has been struggling to find the perfect black handbag to fit an iPad, folders, books anda large wallet, perhaps with the option to wear cross-body.

The main cause of HDP anxiety, I suspect, stems from the irreversibility and economic significance of the decision amid what behavioral economists call “conditions of uncertainty.” That is to say, once you plunk down $2,000 or more for a bag and start wearing it, you can’t return it—and there’s no way of knowing whether everybody else on the street will simultaneously decide to start sporting the same style (or, worse, counterfeit versions of it). As we have seen with the Prada backpack, the Fendi Baguette, the Chloé Paddington, the Goyard tote, the Balenciaga City bag and countless others, an “It” handbag can be an unpredictable and bittersweet phenomenon.

In a modern, mobile world, there’s also something deeper going on with women and their bags, according to Judith Clark, professor of fashion and museology at the London College of Fashion. “On one level, it’s this banal thing: How do I choose a handbag?” said Ms. Clark, who curated the permanent collection at the recently opened Simone Handbag Museum in Seoul. “But it’s also a very intimate decision, having to do with the privacy that goes along with the inside of a bag.” In picking a bag, we are in essence showing the world how we pay respect to the contents of our lives, and perhaps even ourselves.

Kathleen Vohs, a University of Minnesota marketing professor who studies decision-making, said that the likelihood of paralysis rises when “people think that a decision reflects who they really are.” (Ms. Vohs is the lead author of the paper that President Obama cited in a recent Vanity Fair profile to explain why he only wears blue or gray suits. Apparently wasting mental energy on less important decisions impedes the ability to make crucial ones.)

Getting past HDP can take time. Rebecca Sinn, a 32-year-old editor at Glamour magazine, said that she has been eyeing the neat, top-handled Yves Saint Laurent Muse II bag for more than three years but just can’t pull the trigger. She likened buying the bag, which costs about $1,500, to “committing to adulthood,” something that she’s not quite ready to do.

Ask yourself: Will I love this bag no matter what?

When my friend Julie, a stylist, began emailing me pictures of the large Proenza Schouler PS1, we started a lively debate over whether the bag was still “It”—and if it was, whether this was a good thing or not. I had seen versions of it on the flash-sale website Gilt.com, which is a mixed blessing for bag enthusiasts. On one hand, it means you can get the bag for about 30% off. On the other, the discounting is a signal that the bag could be nearing the end of its “It” run. I’ve carried bags past their invisible expiration date; it’s a feeling akin to betting on the wrong horse at the Kentucky Derby.

“When you are considering spending that much money, you have to remove the question of trends from your mind,” advised Julie as I waffled over the PS1. “Ask yourself: Will I love this no matter what?” She and I both decided that we would not love this bag no matter what. Instead, Julie bought a Céline Luggage Tote a couple of months ago.

Ms. Zucher, the matchmaker, has been torn between three options: a Miu Miu tote ($1,495), a large Chanel shopping tote (about $3,000) and a YSL Cabas Chyc “East West” bag ($2,450). She finally chose the YSL because she felt it had the most “longevity.”

That quality might be more easily found in brands that have dispensed with the quest for It-ness, but still make bags that aren’t boring. Each year, Italian leathergoods company Valextra makes only two to three new models of its bags, which are scratch- and stain- resistant and highly functional. Chief executive Emanuele Carminati Molina sees them as “the expression of an enduring aesthetic.”

Longevity is also what French designer Myriam Schaefer is seeking in her bags. Ms. Schaefer—known for helping to design the Balenciaga City bag, which was an “It” sensation over a decade ago—has gone in a discreet and minimal direction with the eponymous collection that she started in late 2011. “I was tired of these bags that cost a fortune and that everybody’s copying after three months,” she said. “With my bags you can use them for 10 or 20 years like my mother and grandmother did.”

That sounds like a promising proposition, although committing to a handbag for 20 years is a little overwhelming. Maybe this is the root cause of my anxiety: knowing that my track record is spotty. Every single time I have bought an expensive bag, I envisioned us having a long future together, then soon tired of it.

I recently abandoned my plan to buy Givenchy’s Nightingale bag after seeing three women carrying them in Las Vegas. For now, I’m still carrying that canvas tote, but getting closer and closer to curing myself of HDP.

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